Polycaprolactone (PCL) and dimethylsulfone (DMSO2) composites can tailor the properties of scaffold materials, allowing their use in bone tissue engineering. With an increase in DMSO2 content, the modulus of the material increases but not the yield strength. In order to increase yield strength, a binder was added. However, the optimization of the content and the mixing process of the binder were not optimized in the previous studies. In this study, gamma-methacryloxypropyltrimethoxysilane (A-174) was used as a binder to increase the strength of a composite. Four different mixing processes were employed based on the binder mixing sequence. The binders with content of 0, 0.4, 0.5, 0.7, and 1.5 phr were employed. The yield strengths of composites were investigated in terms of the binder mixing sequence and binder content. When the binder and DMSO2 particle fillers were premixed in the PCL matrix consisting of a DMSO2 filler and an A-174 binder system, the filler surface was coated smoothly and uniformly, and less agglomeration occurred. The yield strength of the composites with the appropriate mixing sequence was 36.71% higher than that of the specimen without a binder, which was attributed to the improved adhesion between the matrix and fillers. Upon increasing the binder content, elongation and tearing of the matrix surface were observed in the cross-sections after yield tests; however, the weakening of mechanical anchoring was caused by excessive binder content, and filler debonding was observed on the surface. Because of the use of the A-174 silane binder at a concentration of 0.5 phr and the premixing of the binder and filler, the highest performance in terms of strength improvement of a PCL-20 wt % DMSO2 composite was achieved.